3(S)-(Benzofuran-6-yl)-3-[benzyl-(1(R)-phenyl-ethyl)-amino]-propionic acid ethyl ester → 3(S)-Amino-3-(2,3-dihydro-benzofuran-6-yl)-propionic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH2:5][C@@H:6]([C:23]1[CH:31]=[CH:30][C:26]2[CH:27]=[CH:28][O:29][C:25]=2[CH:24]=1)[N:7](CC1C=CC=CC=1)[C@@H](C1C=CC=CC=1)C)[CH3:2]>CCO.O.CC(O)=O>[CH2:1]([O:3][C:4](=[O:32])[CH2:5][C@H:6]([NH2:7])[C:23]1[CH:31]=[CH:30][C:26]2[CH2:27][CH2:28][O:29][C:25]=2[CH:24]=1)[CH3:2]Participants
3
Procedure
A mixture of the dibenzylamine 3-5 (1.19 g, 2.78 mmol) in EtOH/H2O/AcOH (26 mL/3 mL/1.0 mL) was degassed with argon and treated with Pd(OH)2 (1.19 g). The mixture was placed under 1 atm of H2. After stirring for 18 h, the mixture was diluted with EtOAc, and filtered through celite. The filtrate was concentrated and the residue purified by flash chromatography (10% ethyl acetate/dichloromethane) to give the ester 3-6 as a white solid.
Workup
- customwas degassed with argon
- additiontreated with Pd(OH)2 (1.19 g)
- additionthe mixture was diluted with EtOAc
- filtrationfiltered through celite
- concentrationThe filtrate was concentrated
- customthe residue purified by flash chromatography (10% ethyl acetate/dichloromethane)
Sources & evidence
- ORD record
- ord-04f47ce171894a2285ae9e307713c970
- Source dataset
- uspto-grants-2000_05
- Patent number
- US06066648
Reaction notes
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